(4-Nitrophenyl)(1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate.

In the crystal structure of the title compound, C(18)H(17)N(3)O(3)·H(2)O, the mol-ecules are linked by O-H⋯O and O-H⋯N hydrogen bonds, resulting in a chain along the a axis. The crystal structure is stabilized by weak inter-molecular C-H⋯π (ring) hydrogen bonds and aromatic π⋯π stacking inter-actions [centroid-centroid distance = 3.902 (1) Å] between the pyrimidino rings of the quinazoline system. The tricyclic quinazoline fragment is almost planar (rms deviation = 0.0139 Å) with the two methylene C atoms of the pyrrolo ring deviating by 0.148 (2) and -0.081 (3) Å from the plane through the other atoms. The 4-nitrophenyl ring makes a dihedral angle of 12.55 (7)° with the tricyclic ring system.

Related literature

For general background to tricyclic quinazoline alkaloids, see: Shakhidoyatov et al. (1988 ▶). For the synthesis of 1,2,3,9-tetra­hydro-pyrrolo­[2,1-b]quinazoline, see: Jahng et al. (2008 ▶). For the physiological activity of quinazoline derivatives, see: Al-Shamma et al. (1981 ▶); Yunusov et al. (1978 ▶).

Experimental

Crystal data

C18H17N3O3·H2O

M = 341.36

Triclinic,

a = 6.2459 (7) Å

b = 11.4629 (11) Å

c = 11.8400 (13) Å

α = 91.932 (8)°

β = 95.589 (9)°

γ = 104.747 (9)°

V = 814.37 (15) Å3

Z = 2

Cu Kα radiation

μ = 0.83 mm−1

T = 295 K

0.50 × 0.35 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.793, T max = 1.000

4649 measured reflections

2867 independent reflections

2076 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.03

2867 reflections

238 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021775/rk2278sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021775/rk2278Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021775/rk2278Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H17N3O3·H2O	Z = 2
Mr = 341.36	F(000) = 360
Triclinic, P1	Dx = 1.392 Mg m−3
Hall symbol: -P 1	Melting point = 473(2)–474(2) K
a = 6.2459 (7) Å	Cu Kα radiation, λ = 1.54180 Å
b = 11.4629 (11) Å	Cell parameters from 1912 reflections
c = 11.8400 (13) Å	θ = 3.8–66.8°
α = 91.932 (8)°	µ = 0.83 mm−1
β = 95.589 (9)°	T = 295 K
γ = 104.747 (9)°	Prism, light-yellow
V = 814.37 (15) Å3	0.50 × 0.35 × 0.15 mm

Oxford Diffraction Xcalibur Ruby diffractometer	2867 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2076 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.2576 pixels mm-1	θmax = 66.9°, θmin = 3.8°
ω–scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.793, Tmax = 1.000	l = −11→14
4649 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0752P)2 + 0.0389P] where P = (Fo2 + 2Fc2)/3
2867 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.8540 (2)	0.61715 (12)	0.92847 (12)	0.0555 (4)
O2	0.6598 (3)	1.09493 (15)	1.24380 (17)	0.0991 (6)
O3	0.3240 (3)	0.99048 (18)	1.24831 (17)	0.1005 (6)
N1	0.3825 (2)	0.45278 (13)	0.71834 (12)	0.0471 (4)
C2	0.5561 (3)	0.54174 (16)	0.71298 (14)	0.0427 (4)
N3	0.7234 (2)	0.54380 (13)	0.65065 (13)	0.0487 (4)
C4	0.7416 (3)	0.44111 (18)	0.58074 (16)	0.0537 (5)
H4A	0.8783	0.4197	0.6060	0.064*
H4B	0.7473	0.4624	0.5023	0.064*
C4A	0.5454 (3)	0.33484 (17)	0.58861 (15)	0.0475 (4)
C5	0.5291 (4)	0.22532 (19)	0.53039 (18)	0.0636 (6)
H5A	0.6415	0.2178	0.4868	0.076*
C6	0.3493 (4)	0.1273 (2)	0.5359 (2)	0.0700 (6)
H6A	0.3414	0.0545	0.4964	0.084*
C7	0.1821 (4)	0.13746 (18)	0.59957 (19)	0.0643 (6)
H7A	0.0599	0.0719	0.6028	0.077*
C8	0.1959 (3)	0.24550 (17)	0.65902 (17)	0.0558 (5)
H8A	0.0828	0.2518	0.7027	0.067*
C8A	0.3761 (3)	0.34467 (16)	0.65443 (14)	0.0451 (4)
C9	0.5996 (3)	0.65999 (15)	0.78287 (15)	0.0457 (4)
H9A	0.4710	0.6940	0.7698	0.055*
C10	0.8016 (4)	0.74163 (18)	0.73443 (18)	0.0609 (5)
H10A	0.7562	0.8017	0.6888	0.073*
H10B	0.9129	0.7828	0.7955	0.073*
C11	0.8949 (3)	0.65817 (18)	0.66131 (18)	0.0575 (5)
H11A	0.9194	0.6898	0.5874	0.069*
H11B	1.0345	0.6483	0.6980	0.069*
C12	0.6388 (3)	0.63750 (15)	0.90930 (14)	0.0433 (4)
H12A	0.5295	0.5631	0.9240	0.052*
C13	0.6112 (3)	0.73811 (15)	0.98840 (14)	0.0425 (4)
C14	0.7810 (3)	0.83964 (17)	1.02340 (17)	0.0563 (5)
H14A	0.9196	0.8485	0.9973	0.068*
C15	0.7481 (3)	0.92825 (17)	1.09669 (18)	0.0611 (5)
H15A	0.8630	0.9967	1.1193	0.073*
C16	0.5446 (3)	0.91394 (16)	1.13547 (16)	0.0510 (5)
C17	0.3738 (3)	0.8124 (2)	1.10522 (19)	0.0652 (6)
H17A	0.2373	0.8026	1.1340	0.078*
C18	0.4091 (3)	0.72560 (19)	1.03133 (19)	0.0619 (6)
H18A	0.2942	0.6568	1.0098	0.074*
N19	0.5065 (4)	1.00649 (17)	1.21455 (16)	0.0689 (5)
H1	0.878 (4)	0.600 (3)	1.006 (3)	0.113 (10)*
O1W	0.0490 (2)	0.43285 (14)	0.85779 (12)	0.0573 (4)
H1W	0.151 (4)	0.444 (2)	0.812 (2)	0.081 (8)*
H2W	−0.024 (4)	0.490 (3)	0.864 (2)	0.107 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0543 (8)	0.0736 (9)	0.0481 (8)	0.0331 (7)	0.0083 (6)	0.0005 (7)
O2	0.1175 (15)	0.0596 (10)	0.1127 (15)	0.0132 (10)	0.0153 (11)	−0.0336 (10)
O3	0.0964 (13)	0.1053 (13)	0.1106 (15)	0.0431 (11)	0.0318 (11)	−0.0328 (11)
N1	0.0458 (8)	0.0505 (9)	0.0447 (8)	0.0111 (7)	0.0108 (7)	−0.0062 (7)
C2	0.0426 (9)	0.0493 (10)	0.0379 (9)	0.0156 (8)	0.0039 (7)	0.0014 (7)
N3	0.0474 (8)	0.0537 (9)	0.0458 (9)	0.0118 (7)	0.0136 (7)	−0.0008 (7)
C4	0.0515 (11)	0.0680 (12)	0.0460 (11)	0.0219 (9)	0.0116 (8)	−0.0019 (9)
C4A	0.0520 (10)	0.0563 (11)	0.0376 (9)	0.0212 (9)	0.0036 (8)	−0.0013 (8)
C5	0.0705 (14)	0.0696 (14)	0.0563 (12)	0.0293 (11)	0.0087 (10)	−0.0112 (10)
C6	0.0858 (16)	0.0566 (12)	0.0676 (14)	0.0239 (12)	0.0001 (12)	−0.0163 (11)
C7	0.0711 (14)	0.0504 (11)	0.0652 (13)	0.0071 (10)	0.0025 (11)	−0.0043 (10)
C8	0.0588 (12)	0.0556 (11)	0.0521 (12)	0.0125 (9)	0.0103 (9)	−0.0020 (9)
C8A	0.0498 (10)	0.0481 (10)	0.0381 (9)	0.0147 (8)	0.0038 (8)	0.0000 (7)
C9	0.0472 (10)	0.0466 (9)	0.0443 (10)	0.0153 (8)	0.0032 (8)	−0.0012 (8)
C10	0.0749 (14)	0.0518 (11)	0.0520 (12)	0.0069 (10)	0.0126 (10)	0.0050 (9)
C11	0.0522 (11)	0.0611 (12)	0.0553 (12)	0.0051 (9)	0.0111 (9)	0.0072 (9)
C12	0.0404 (9)	0.0465 (9)	0.0447 (10)	0.0130 (8)	0.0097 (7)	−0.0007 (8)
C13	0.0394 (9)	0.0471 (9)	0.0412 (9)	0.0121 (8)	0.0042 (7)	0.0001 (7)
C14	0.0465 (10)	0.0555 (11)	0.0630 (13)	0.0028 (9)	0.0182 (9)	−0.0053 (9)
C15	0.0610 (12)	0.0463 (10)	0.0670 (13)	−0.0034 (9)	0.0132 (10)	−0.0087 (9)
C16	0.0609 (12)	0.0478 (10)	0.0474 (10)	0.0211 (9)	0.0050 (9)	−0.0035 (8)
C17	0.0436 (11)	0.0751 (14)	0.0766 (14)	0.0156 (10)	0.0139 (10)	−0.0211 (11)
C18	0.0382 (10)	0.0673 (12)	0.0728 (14)	0.0025 (9)	0.0107 (9)	−0.0252 (10)
N19	0.0874 (14)	0.0598 (11)	0.0644 (12)	0.0304 (11)	0.0071 (10)	−0.0099 (9)
O1W	0.0554 (9)	0.0704 (9)	0.0539 (8)	0.0256 (7)	0.0187 (7)	0.0049 (7)

O1—C12	1.420 (2)	C9—C12	1.534 (2)
O1—H1	0.95 (3)	C9—C10	1.540 (3)
O2—N19	1.217 (2)	C9—H9A	0.9800
O3—N19	1.216 (2)	C10—C11	1.527 (3)
N1—C2	1.294 (2)	C10—H10A	0.9700
N1—C8A	1.420 (2)	C10—H10B	0.9700
C2—N3	1.333 (2)	C11—H11A	0.9700
C2—C9	1.513 (2)	C11—H11B	0.9700
N3—C4	1.451 (2)	C12—C13	1.515 (2)
N3—C11	1.459 (2)	C12—H12A	0.9800
C4—C4A	1.505 (3)	C13—C14	1.380 (2)
C4—H4A	0.9700	C13—C18	1.382 (2)
C4—H4B	0.9700	C14—C15	1.381 (3)
C4A—C5	1.387 (3)	C14—H14A	0.9300
C4A—C8A	1.398 (2)	C15—C16	1.366 (3)
C5—C6	1.380 (3)	C15—H15A	0.9300
C5—H5A	0.9300	C16—C17	1.374 (3)
C6—C7	1.372 (3)	C16—N19	1.471 (2)
C6—H6A	0.9300	C17—C18	1.377 (3)
C7—C8	1.383 (3)	C17—H17A	0.9300
C7—H7A	0.9300	C18—H18A	0.9300
C8—C8A	1.388 (3)	O1W—H1W	0.86 (3)
C8—H8A	0.9300	O1W—H2W	0.89 (3)
C12—O1—H1	108.1 (17)	C11—C10—H10A	110.5
C2—N1—C8A	115.94 (14)	C9—C10—H10A	110.5
N1—C2—N3	126.93 (16)	C11—C10—H10B	110.5
N1—C2—C9	123.07 (15)	C9—C10—H10B	110.5
N3—C2—C9	109.97 (15)	H10A—C10—H10B	108.7
C2—N3—C4	123.89 (15)	N3—C11—C10	104.22 (14)
C2—N3—C11	114.25 (15)	N3—C11—H11A	110.9
C4—N3—C11	121.82 (14)	C10—C11—H11A	110.9
N3—C4—C4A	110.24 (14)	N3—C11—H11B	110.9
N3—C4—H4A	109.6	C10—C11—H11B	110.9
C4A—C4—H4A	109.6	H11A—C11—H11B	108.9
N3—C4—H4B	109.6	O1—C12—C13	112.19 (14)
C4A—C4—H4B	109.6	O1—C12—C9	107.19 (13)
H4A—C4—H4B	108.1	C13—C12—C9	113.63 (14)
C5—C4A—C8A	118.79 (18)	O1—C12—H12A	107.9
C5—C4A—C4	120.53 (17)	C13—C12—H12A	107.9
C8A—C4A—C4	120.68 (16)	C9—C12—H12A	107.9
C6—C5—C4A	121.3 (2)	C14—C13—C18	118.21 (17)
C6—C5—H5A	119.4	C14—C13—C12	123.21 (15)
C4A—C5—H5A	119.4	C18—C13—C12	118.53 (16)
C7—C6—C5	119.88 (19)	C13—C14—C15	120.99 (17)
C7—C6—H6A	120.1	C13—C14—H14A	119.5
C5—C6—H6A	120.1	C15—C14—H14A	119.5
C6—C7—C8	119.8 (2)	C16—C15—C14	119.12 (18)
C6—C7—H7A	120.1	C16—C15—H15A	120.4
C8—C7—H7A	120.1	C14—C15—H15A	120.4
C7—C8—C8A	120.87 (19)	C15—C16—C17	121.54 (17)
C7—C8—H8A	119.6	C15—C16—N19	120.08 (18)
C8A—C8—H8A	119.6	C17—C16—N19	118.35 (18)
C8—C8A—C4A	119.37 (17)	C16—C17—C18	118.45 (18)
C8—C8A—N1	118.37 (16)	C16—C17—H17A	120.8
C4A—C8A—N1	122.25 (16)	C18—C17—H17A	120.8
C2—C9—C12	109.34 (14)	C17—C18—C13	121.65 (18)
C2—C9—C10	103.65 (14)	C17—C18—H18A	119.2
C12—C9—C10	114.74 (15)	C13—C18—H18A	119.2
C2—C9—H9A	109.6	O3—N19—O2	123.18 (19)
C12—C9—H9A	109.6	O3—N19—C16	118.45 (19)
C10—C9—H9A	109.6	O2—N19—C16	118.4 (2)
C11—C10—C9	106.12 (15)	H1W—O1W—H2W	118 (3)

Cg1 and Cg2 are the centroids of the N1,C2,N3,C4,C4A,C8A and C4A,C5–C8,C8A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N1	0.86 (2)	1.89 (3)	2.751 (2)	174 (2)
O1W—H2W···O1i	0.89 (3)	1.97 (3)	2.835 (2)	162 (2)
O1—H1···O1Wii	0.95 (4)	1.71 (3)	2.660 (2)	173 (3)
C4—H4B···Cg1iii	0.97	2.92	3.634 (2)	131
C11—H11A···Cg2iii	0.97	2.94	3.681 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,C2,N3,C4,C4A,C8A and C4A,C5–C8,C8A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N1	0.86 (2)	1.89 (3)	2.751 (2)	174 (2)
O1W—H2W⋯O1i	0.89 (3)	1.97 (3)	2.835 (2)	162 (2)
O1—H1⋯O1Wii	0.95 (4)	1.71 (3)	2.660 (2)	173 (3)
C4—H4B⋯Cg1iii	0.97	2.92	3.634 (2)	131
C11—H11A⋯Cg2iii	0.97	2.94	3.681 (2)	134

Symmetry codes: (i) ; (ii) ; (iii) .